As the method of producing adamantanepolyols, Japanese Patent Application Laid-Open No. 2-104553 discloses a method using chromic acid. Japanese Patent Application Laid-Open No. 3-118342 and Japanese Patent No. 2678784 teach methods of hydrolyzing a brominated adamantane. Japanese Patent Application Laid-Open Nos. 8-38909, 9-327626 and 10-286467 disclose oxidization of adamantane compounds by oxygen in the presence of imide compound catalyst. Japanese Patent Application Laid-Open No.9-87216 discloses a metalloporphyrin-catalyzed oxidization of adamantane compounds by air. Japanese Patent Application Laid-Open No. 5-51334 uses ruthenium catalysts and peroxy acids. J. Am. Chem. Soc., 111, 6749 (1989) discloses a method of using dioxirane derivatives. However, the major problems of the proposed methods are in the complicated reaction systems and low yields.
An object of the present invention is to provide a method of selectively producing adamantanols from adamantane compounds in high yields.
Another object of the present invention is to provide a method of selectively producing adamantanols from adamantane compounds in high yields, where the extraction of adamantanediols is easy.
Still another object of the present invention is to provide a method of selectively producing adamantanols from adamantane compounds in high yields, where ruthenium compound is efficiently recovered.